Pyridine, hydrofluoride (1:1) → methyl(11R,12S,13E,15S)-9-(N-benzyloxycarbonylphenylalanyloxy)-11,15-dihydroxy-7-thiaprosta-8,13-dienoate

HRID 3035

Reaktionsgleichung

Reaktionsgleichung von HRID 3035
N1C=CC=CC=1.F.[CH3:8][O:9][C:10](=[O:68])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][S:16][C:17]1[C@@H:21](/[CH:22]=[CH:23]/[C@@H:24]([O:30][Si](C(C)(C)C)(C)C)[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C@H:20]([O:38][Si](C(C)(C)C)(C)C)[CH2:19][C:18]=1[O:46][C:47](=[O:67])[C@H:48]([CH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)[NH:49][C:50]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51]>>[CH3:8][O:9][C:10](=[O:68])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][S:16][C:17]1[C@@H:21](/[CH:22]=[CH:23]/[C@@H:24]([OH:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C@H:20]([OH:38])[CH2:19][C:18]=1[O:46][C:47](=[O:67])[C@H:48]([CH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)[NH:49][C:50]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51]

Komponenten

3

Edukt 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 22883810methyl(11R,12S,13E,15S)-9-(N-benzyloxycarbonylphenylalanyloxy)-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoate

Produkt 1

HCID 22883811methyl(11R,12S,13E,15S)-9-(N-benzyloxycarbonylphenylalanyloxy)-11,15-dihydroxy-7-thiaprosta-8,13-dienoateAusbeute 51 %

Versuchsvorschrift

Using as the material and reagent a hydrogen fluoride-pyridine solution (0.3 ml) and methyl(11R,12S,13E,15S)-9-(N-benzyloxycarbonylphenylalanyloxy)-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoate (140 mg), methyl(11R,12S,13E,15S)-9-(N-benzyloxycarbonylphenylalanyloxy)-11,15-dihydroxy-7-thiaprosta-8,13-dienoate (53 mg, 51%) was obtained.

Quellen und Nachweise

ORD-Eintrag
ord-d5c0f98feabe41e293e98aa397fcf97a
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731452

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